7a-acetoxy-1,1,4a,5,6,8-hexamethyl-1,2,3,4-tetrahydro-9H-xanthene | 19048-46-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 7a-acetoxy-1,1,4a,5,6,8-hexamethyl-1,2,3,4-tetrahydro-9H-xanthene
• 英文别名: 7-acetoxy-1,1,4a,5,6,8-hexamethyl-1,2,3,4,4a,9a-hexahydro-xanthene；7-Acetoxy-1,1,4a,5,6,8-hexamethyl-1,2,3,4-tetrahydro-9h-xanthene；(1,3,4,8,8,10a-hexamethyl-6,7,8a,9-tetrahydro-5H-xanthen-2-yl) acetate
• CAS: 19048-46-5
• 化学式: C₂₁H₃₀O₃
• 分子量: 330.467
• InChiKey: KGROHYHDDKBTOC-UHFFFAOYSA-N

物化性质

• 熔点：
  138-139 °C
• 沸点：
  418.8±45.0 °C(Predicted)
• 密度：
  1.036±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  芳樟醇 在 Tseokar-10 作用下， 以 吡啶 、 正庚烷 为溶剂， 反应 6.5h， 生成 7a-acetoxy-1,1,4a,5,6,8-hexamethyl-1,2,3,4-tetrahydro-9H-xanthene
  参考文献：
  名称：

  摘要：

  alpha-Tocopherol analogs with double bond-containing side chains were synthesized by condensation of trimethylhydroquinone with optically active (3R/S,4S)-3,4,8-trimethylnona-1,7-dien-3-ol and linalool in the presence of the zeolite-containing Tseokar-10 aluminosilicate. Ozonolysis of these compounds gave the corresponding chromans with omega-formyl or (after hydride reduction) omega-hydroxyl groups in the side chain.

  DOI：

  10.1023/a:1015086326009

文献信息

• A Convenient Access to (All-<i>rac</i>)-α-Tocopherol Acetate from Linalool and Dihydromyrcene
  作者：Vincent Gembus、Nathalie Sala-Jung、Daniel Uguen

  DOI：10.1246/bcsj.82.829

  日期：2009.7.15

  Refluxing trimethylhydroquinone 2 in 10:1 dodecane/CH2Cl2 with linalool 3b (two-fold excess) and camphorsulfonic acid, then treating the crude condensation product (consisting of a mixture of the chromanols 1b and 1c, alongside the tricyclic compounds 9 and 10) sequentially with Ac2O and m-CPBA afforded, after removal by column chromatography of the 9/10 acetates, a mixture of the regioisomeric epoxides 1jOAc and 1kOAc (ratio 9:1, total 60%). Treatment of this mixture with Al(O-i-Pr)3 followed by CuI-catalysed Wurtz coupling of the acetates of the resulting allylic alcohols with citronellylmagnesium chloride 12a, and finally hydrogenation then provided the title acetate (overall 46% from 2).

  将三甲基氢醌 2 在 10:1 的十二烷/二氯甲烷中与过量的香叶醇 3b 和樟脑磺酸催化剂重流，随后对粗凝聚物（由克罗曼醇 1b 和 1c 以及三环化合物 9 和 10 的混合物组成）依次用醋酸酐和对氯苯甲酸酯处理，经过柱层析去除 9/10 乙酸酯后，得到区域异构体环氧化物 1jOAc 和 1kOAc 的混合物（比例为 9:1，总产率 60%）。将该混合物与 Al(O-i-Pr)3 处理，然后用 CuI 催化的沃尔茨偶联反应将得到的烯醇乙酸酯与香柠檬醇镁氯化物 12a 偶联，最后进行氢化，便得到标题乙酸酯（总体产率为 46%）。
• ——
  作者：V. N. Odinokov、A. Yu. Spivak、G. A. Emelianova、B. I. Kutepov、L. M. Khalilov

  DOI：10.1023/a:1015086326009

  日期：——

  alpha-Tocopherol analogs with double bond-containing side chains were synthesized by condensation of trimethylhydroquinone with optically active (3R/S,4S)-3,4,8-trimethylnona-1,7-dien-3-ol and linalool in the presence of the zeolite-containing Tseokar-10 aluminosilicate. Ozonolysis of these compounds gave the corresponding chromans with omega-formyl or (after hydride reduction) omega-hydroxyl groups in the side chain.